Oxidation Of Organic Compound Utilizing Gaseous Oxygen Patents (Class 568/431)
  • Publication number: 20150111976
    Abstract: The present disclosure provides a series of new and improved porous polyamide aerogels derived from multifunctional aromatics that combine the high mechanical strength of aramids with the pore structure of aerogels. The polyamide aerogels have a hyperbranched structure, relatively low density, high porosity and may be derived from functionalized monomers having more aromatic groups than functional groups. The present disclosure also provides a new method for producing the porous polyamide aerogels by polymerizing an aromatic multifunctional carboxylic acid or a ferrocene multifunctional carboxylic acid with a polyfunctional aromatic isocyanate at moderate reaction conditions followed by drying with liquid CO2. Also disclosed are various methods of use of these polyamide aerogels in a variety of applications.
    Type: Application
    Filed: October 31, 2014
    Publication date: April 23, 2015
    Inventors: Nicholas Leventis, Chariklia Sotiriou-Leventis, Malik Adnan Saeed
  • Patent number: 8969603
    Abstract: Provided are processes for the oxidative cleavage of a double bond in an unsaturated carboxylic acid. The process includes contacting the unsaturated carboxylic acid with a mild oxidizing agent and agitating the unsaturated carboxylic acid and the mild oxidizing agent for a time sufficient to cleave a double bond of the unsaturated carboxylic acid and produce a product comprising an aldehyde. The process is typically carried out in a mill, such as a ball, hammer, attrition, or jet mill.
    Type: Grant
    Filed: January 23, 2014
    Date of Patent: March 3, 2015
    Assignee: University of Central Florida Research Foundation, Inc.
    Inventor: Richard G. Blair
  • Publication number: 20140200359
    Abstract: Provided are processes for the oxidative cleavage of a double bond in an unsaturated carboxylic acid. The process includes contacting the unsaturated carboxylic acid with a mild oxidizing agent and agitating the unsaturated carboxylic acid and the mild oxidizing agent for a time sufficient to cleave a double bond of the unsaturated carboxylic acid and produce a product comprising an aldehyde. The process is typically carried out in a mill, such as a ball, hammer, attrition, or jet mill.
    Type: Application
    Filed: January 23, 2014
    Publication date: July 17, 2014
    Applicant: University of Central Florida Research Foundation, Inc.
    Inventor: Richard G. Blair
  • Publication number: 20130316938
    Abstract: Provided is class of compounds of formula (I) wherein X, R1, R2 and R3 have the same meaning as given in the specification capable of releasing fragrant compounds in a controlled manner into the surroundings.
    Type: Application
    Filed: December 23, 2011
    Publication date: November 28, 2013
    Applicant: GIVAUDAN S.A.
    Inventors: Corinne Baumgartner, Felix Flachsmann, Philip Kraft
  • Publication number: 20130041175
    Abstract: A process for oxidizing an alkyl-aromatic compound is described. The process includes contacting the alkyl-aromatic compound, a solvent comprising an ionic liquid, a bromine source, a catalyst, and an oxidizing agent in a first reaction zone to produce a first product comprising a first mother liquor and at least one of an aromatic alcohol, an aromatic aldehyde, an aromatic ketone, and an aromatic carboxylic acid.
    Type: Application
    Filed: October 12, 2012
    Publication date: February 14, 2013
    Applicant: UOP LLC
    Inventors: Alakananda Bhattacharyya, Raymond Shih
  • Publication number: 20120232279
    Abstract: The invention concerns processes for oxidizing an alcohol to produce a carbonyl compound. The processes comprise contacting the alcohol with (i) a gaseous mixture comprising oxygen; and (ii) an amine compound in the presence of a catalyst, having the formula: where each of R1-R12 are independently H, alkyl, aryl, CF3, halogen, OR13, SO3R14, C(O)R15, CONR16R17 or CO2R18; each of R13-R18 is independently alkyl or aryl; and Z is alkl or aryl.
    Type: Application
    Filed: March 8, 2012
    Publication date: September 13, 2012
    Applicant: LOS ALAMOS NATIONAL SECURITY, LLC
    Inventors: Susan Kloek Hanson, Louis A. Silks, Ruilian Wu
  • Publication number: 20120220792
    Abstract: Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1˜10:1˜10:1˜10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.
    Type: Application
    Filed: July 30, 2010
    Publication date: August 30, 2012
    Inventors: Shengming Ma, Jinxian Liu, Jinqiang Kuang, Yu Liu, Yuli Wang, Qiong Yu, Weiming Yuan, Suhua Li, Bo Chen, Jiajia Cheng, Baoqiang Wan, Juntao Ye, Shichao Yu
  • Patent number: 7956203
    Abstract: Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: June 7, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Vladimir Grushin, Walter Partenheimer, Leo E. Manzer
  • Patent number: 7868201
    Abstract: A process for the oxidation of hydrocarbons comprises contacting the hydrocarbon with an oxygen-containing gas in the presence of a catalyst comprising a microporous solid support, preferably a zeolite, having from 8- to 12-ring open windows and comprising non-framework metal cations selected from manganese, iron, cobalt, vanadium, chromium, copper, nickel, and ruthenium, and mixtures thereof, providing that the oxygen-containing gas does not contain significant amounts of added hydrogen. The catalyst is novel and forms part of the invention. The process may be used for oxidation of alkanes, cycloalkanes, benzene and alkylbenzenes, and is suitable for use in regioselective terminal oxidation of straight chain alkanes and for selective oxidation/separation of p-dialkylbenzenes from an alkylbenzene mixture, for example, p-xylene from an isomeric mixture of xylenes.
    Type: Grant
    Filed: July 1, 2005
    Date of Patent: January 11, 2011
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
  • Publication number: 20100324331
    Abstract: The invention relates to mixed oxide catalysts made of hollow shapes for the catalytic gas phase oxidation of olefins, and to a method for producing the catalysts by applying them as a layer to a carrier made of organic material and removing said organic material. The reaction into aldehydes and carboxylic acids occurs by air or oxygen in the presence of inert gases in different quantity ratios, at elevated temperatures and pressure in the presence of said catalysts.
    Type: Application
    Filed: January 28, 2008
    Publication date: December 23, 2010
    Inventors: Achim Fischer, Werner Burkhardt, Stefan Röder, Klaus Huthmacher
  • Publication number: 20100267988
    Abstract: The invention relates, in general, to an improved process for preparing compounds (e.g., 3-(3-trifluoromethylphenyl)propanal (Compound III, below)), which are key intermediates for the synthesis of cinacalcet, its salts and/or solvates thereof, as well as the use of such compounds prepared by such process for the preparation of cinacalcet and/or its salts or solvates.
    Type: Application
    Filed: June 8, 2007
    Publication date: October 21, 2010
    Applicant: Medichem, S.A.
    Inventors: Tibor Szekeres, Jozsef Repasi, Andras Szabo, Bernardino Mangion
  • Patent number: 7740812
    Abstract: The present invention relates to a method and an apparatus for continuously separating aromatic dialdehyde from a reaction mixture obtained by gas-phase oxidation of dimethylbenzene. The method for continuously separating aromatic dialdehyde includes the steps of congealing aromatic dialdehyde by cooling the gas-phase reaction mixture including the aromatic dialdehyde, which is obtained by gas-phase oxidation of dimethylbenzene, to 5-70° C. and separating the congealed aromatic dialdehyde from the remaining reaction mixture. Using the method and apparatus in accordance with the present invention, aromatic dialdehyde can be effectively and selectively separated from a reaction mixture obtained by gas-phase oxidation of dimethylbenzene in high yield.
    Type: Grant
    Filed: June 2, 2008
    Date of Patent: June 22, 2010
    Assignee: LG Chem, Ltd.
    Inventors: Jong-Hyun Chae, Won-Ho Lee, Dong-Il Lee, Hyun-Kyung Yoon
  • Publication number: 20100130787
    Abstract: Reaction plates for microreactors for performing gas-liquid reactions, which consist of falling-film plates with a surface which has a randomly distributed, unordered fine structure or microstructure.
    Type: Application
    Filed: March 18, 2008
    Publication date: May 27, 2010
    Inventors: Sascha Braune, Stefan Steinhofer
  • Patent number: 7696387
    Abstract: The present invention relates to a novel method for preparing a catalyst for partial oxidation of methylbenzenes, comprising, (a) a step of preparing a solution or slurry of the compounds comprising tungsten; (b) a step of supporting the solution or slurry obtained in the step (a) on inorganic carrier; (c) a step of drying the catalyst obtained in the step (b); and (d) a step of calcining the dried catalyst obtained in the step (c), characterized in that the ratio of the pore volume of inorganic carrier and the volume of the solution or slurry in the step (b) is 1:0.9˜1.1, and the catalyst provides superior aromatic aldehydes selectivity to those prepared by the conventional impregnation or heat evaporation method over a wide range of conversion rate.
    Type: Grant
    Filed: May 17, 2006
    Date of Patent: April 13, 2010
    Assignee: LG Chem, Ltd.
    Inventors: Won Ho Lee, Dong Il Lee, Jong Hyun Chae, Hyun Kyung Yoon
  • Publication number: 20100010269
    Abstract: A reactor for carrying out a heterogeneously catalyzed reaction includes at least first and second reaction zones that are arranged in series and that each include catalytic material, heat transfer zones that are located between said serially arranged reaction zones, and a pulse-generating device, which is arranged to deliver pulses to liquid in the reactor. The reactor allows three-phase reactions to be carried out efficiently and can reduce the impact of deposited reaction by-products on reaction efficiency.
    Type: Application
    Filed: October 5, 2007
    Publication date: January 14, 2010
    Applicant: The University of Bath
    Inventor: Stanislaw Tadeusz Kolaczkowski
  • Patent number: 7538253
    Abstract: The present invention relates to a novel method for preparing a catalyst of the formula (1), WOx wherein, W represents tungsten atom, O represents oxygen atom x represents a value determined by oxidative state of W, for partial oxidation of methylbenzenes, the method comprising: (a) a step of preparing tungsten oxide slurry by wet milling; (b) a step of supporting the slurry obtained in the step (a) on fire-resistance inorganic carrier by impregnation; (c) a step of drying the catalyst obtained in the step (b); and (d) a step of calcining the dried catalyst obtained in the step (c), and can reduce the reaction temperature on the basis of equivalent yield in the preparation of corresponding aromatic aldehyde from methylbenzenes since the catalyst has increased the surface areas compared to the conventional one, and thus has high conversion rate.
    Type: Grant
    Filed: November 21, 2006
    Date of Patent: May 26, 2009
    Assignee: LG Chem Ltd.
    Inventors: Won Ho Lee, Dong Il Lee, Jong Hyun Chae, Hyun Kyung Yoon
  • Patent number: 7429682
    Abstract: A catalyst for gas phase oxidation of methylbenzenes in the presence of molecular oxygen to produce corresponding aromatic aldehydes, a method for preparing the catalyst, and a method for producing aromatic aldehydes from methylbenzenes by using the catalyst. The catalyst comprises a compound represented by the following formula (1): WaXbYcOx ??(1) wherein W represents a tungsten atom, X represents one or more alkali metals selected from the group consisting of Li, Na, K, Rb, and Cs, Y represents one or more elements selected from the group consisting of Fe, Co, Ni, Cu, Mn, Re, Cr, V, Nb, Ti, Zr, Zn, Cd, Y, La, Ce, B, Al, Sn, Mg, Ca, Sr, and Ba, O stands for an oxygen atom, and the ratio of a:b:c is 12:0.001˜1:0˜5.
    Type: Grant
    Filed: November 22, 2006
    Date of Patent: September 30, 2008
    Assignee: LG Chem, Ltd.
    Inventors: Won Ho Lee, Hyun Kyung Yoon, Dong Il Lee, Jong Hyun Chae, Ji Hyang Son, In Kyu Park, Won Jae Lee
  • Patent number: 7423184
    Abstract: A method of making a carbonyl compound comprises contacting a compound comprising a secondary hydroxyl group with a basic metal oxide catalyst at a temperature sufficient to maintain the compound comprising a secondary hydroxyl group in a vapor phase.
    Type: Grant
    Filed: August 29, 2005
    Date of Patent: September 9, 2008
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Hugo Ingelbrecht, Arun Kumar, Ashok Ramakrishnan Menon, Pradeep Nadkarni, Rupesh Pawar
  • Patent number: 7417171
    Abstract: The present invention relates to a method for preparing an aromatic dialdehyde, comprising, a) a step of gas phase oxidation reaction for preparing aromatic dialdehyde from dimethyl benzene; b) a step of separation for selectively recovering crude aromatic dialdehyde of molten phase from the reaction product of the step (a); and c) a step of purification for obtaining highly pure aromatic dialdehyde by purifying said crude aromatic dialdehyde, and a manufacturing system used for the preparation method. The method for preparation of the aromatic dialdehyde according to the present invention is simple, effective, and advantageous in that highly pure aromatic dialdehyde can be continuously prepared.
    Type: Grant
    Filed: December 13, 2006
    Date of Patent: August 26, 2008
    Assignee: LG Chem, Ltd.
    Inventors: Jong Hyun Chae, Won Ho Lee, Dong Il Lee, In Kyu Park, Yong Jin Choe, Sung Kyu Lee, Yeong Dae Kim, Jong Suh Park, Seong Hoon Kang
  • Patent number: 7411099
    Abstract: The present invention provides a liquid phase oxidation of toluene by using catalyst containing manganese (Manganese II acetate) in presence of Lewis acid (Stannous (II) chloride) and a bromide promoter (NaBr), at a temperature of 120° C. and at a pressure of air in the range of 70-400 psig, in presence of carboxylic acid (acetic acid), as a solvent, to obtain high selectivity to benzaldehyde (76%). High activity was obtained with minimum byproducts such as benzoic acid, benzyl alcohol and benzyl acetate.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: August 12, 2008
    Assignee: Council of Scientific & Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, Kalpendra Baburao Rajurkar, Sunil Sopana Tonde, Vilas Hari Rane
  • Publication number: 20080139841
    Abstract: Oxidations of hydrocarbons, cycloalkanes and alkenes, arylalkanes, and a variety of other organic substrates are accomplished by cobalt-N-hydroxysuccinimide co-catalyzed reactions with dioxygen under unusually mild, near ambient conditions of temperature and pressure. The improved safety of the oxidation method and the high yields of product obtained make use of a unique combination of cobalt (II) complexes with N-hydroxysuccinimide. These autoxidation reactions do not have prolonged initiation times. Many of these reactions can be safely performed under normal chemical laboratory conditions and do not require specialized equipment or reagents.
    Type: Application
    Filed: November 2, 2007
    Publication date: June 12, 2008
    Applicant: University of Kansas
    Inventors: Richard S. Givens, Chi Cheng Ma, Daryle H. Busch, Bala Subramaniam, Bhuma Rajagopalan
  • Patent number: 7338918
    Abstract: A catalyst is described which has a catalytically active composition which contains a phase A and a phase B in the form of three-dimensional delimited regions, wherein phase A is a silver-vanadium oxide bronze and phase B a mixed oxide phase based on titanium dioxide and vanadium pentoxide. The catalyst serves to prepare aldehydes, carboxylic acids and/or carboxylic anhydrides from aromatic or heteroaromatic hydrocarbons by gas phase oxidation.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: March 4, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Samuel Neto, Frank Rosowski, Sebastian Storck, Stefan Bauer
  • Publication number: 20080021248
    Abstract: A catalyst for gas phase oxidation of methylbenzenes in the presence of molecular oxygen to produce corresponding aromatic aldehydes, a method for preparing the catalyst, and a method for producing aromatic aldehydes from methylbenzenes by using the catalyst. The catalyst comprises a compound represented by the following formula (1): WaXbYcOx ??(1) wherein W represents a tungsten atom, X represents one or more alkali metals selected from the group consisting of Li, Na, K, Rb, and Cs, Y represents one or more elements selected from the group consisting of Fe, Co, Ni, Cu, Mn, Re, Cr, V, Nb, Ti, Zr, Zn, Cd, Y, La, Ce, B, Al, Sn, Mg, Ca, Sr, and Ba, O stands for an oxygen atom, and the ratio of a:b:c is 12:0.001˜1:0˜5.
    Type: Application
    Filed: November 22, 2006
    Publication date: January 24, 2008
    Inventors: Won Ho Lee, Hyun Kyung Yoon, Dong Il Lee, Jong Hyun Chae, Ji Hyang Son, In Kyu Park, Won Jae Lee
  • Publication number: 20070213566
    Abstract: The present invention provides a liquid phase oxidation of toluene by using catalyst containing manganese (Manganese II acetate) in presence of Lewis acid (Stannous (II) chloride) and a bromide promoter (NaBr), at a temperature of 120° C. and at a pressure of air in the range of 70-400 psig, in presence of carboxylic acid (acetic acid), as a solvent, to obtain high selectivity to benzaldehyde (76%). High activity was obtained with minimum byproducts such as benzoic acid, benzyl alcohol and benzyl acetate.
    Type: Application
    Filed: September 20, 2006
    Publication date: September 13, 2007
    Inventors: Raghunath Vitthal Chaudhari, Kalpendra Baburao Rajurkar, Sunil Sopana Tonde, Vilas Hari Rane
  • Patent number: 7208634
    Abstract: A method for preparing an aldehyde or ketone by oxidizing a primary or secondary alcohol in the presence of a nitroxyl radical compound and a co-oxidant in an organic solvent, which process is characterized in using an organic N-bromoamide compound or a combination of N-chlorosuccinimide and a compound having bromide ion as the co-oxidant.
    Type: Grant
    Filed: December 1, 2005
    Date of Patent: April 24, 2007
    Assignee: Daiso Co., Ltd.
    Inventors: Kimitaka Igi, Makoto Hirata, Masafumi Mikami
  • Patent number: 7189882
    Abstract: The present invention provides an improved process for the liquid phase oxidation of toluene to benzaldehyde with high selectivity and good activity in an organic acid medium using a catalyst system consisting of transition metal/metals and bromide as a promoter in the presence of lean oxygen.
    Type: Grant
    Filed: December 23, 2005
    Date of Patent: March 13, 2007
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raghunath Vittal Chaudhari, Vilas Hari Rane, Amit Arwind Deshmukh, Sunil Sadashiv Divekar
  • Patent number: 7166751
    Abstract: The object of the present invention is to provide a method for manufacturing cycloalkanol and/or cycloalkanone with favorable selectivity coefficient by oxidizing cycloalkane with favorable degree of conversion. In the present invention, cycloalkane is oxidized with oxygen in the presence of a catalyst such that gold is supported on ceric oxide. Said oxidation is preferably performed in the presence of a free-radical initiator and the free-radical initiator is preferably 2,2?-azobis(isobutyronitrile).
    Type: Grant
    Filed: March 28, 2006
    Date of Patent: January 23, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Avelino Corma, Jose Manuel Lopez Nieto
  • Patent number: 7005542
    Abstract: The present invention provides: a production process for a catalyst for synthesis of an unsaturated aldehyde and/or an unsaturated carboxylic acid, which production process is suitable for producing the catalyst with good reproducibility, wherein the catalyst is excellent in activity, selectivity, and physical strength; this catalyst; and a production process for the unsaturated aldehyde and/or the unsaturated carboxylic acid by using this catalyst.
    Type: Grant
    Filed: February 5, 2003
    Date of Patent: February 28, 2006
    Assignee: Nippon Shokubai Co., Ltd.
    Inventor: Hiromi Yunoki
  • Patent number: 6790997
    Abstract: The invention relates to a process for the preparation of carbonyl compounds by the oxidation of alcohols in the presence of osmium compounds as catalysts in water or a solvent mixture containing water.
    Type: Grant
    Filed: July 23, 2002
    Date of Patent: September 14, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Markus Eckert, Hans-Christian Militzer, Matthias Beller, Christian Döbler, Gerald Mehltretter, Uta Sundermeier
  • Patent number: 6759550
    Abstract: The present invention pertains to an improved method of oxidizing substituted aromatic compounds (such as p xylene) to their corresponding aromatic acids (such as terephthalic acid). The improvement involves carrying out the oxidation reaction in an aqueous medium, wherein the aqueous medium contains at least 30 percent water, preferably up to 30 percent surfactant and preferably a low molecular weight material containing a hydrophilic end group as a co-surfactant. The reaction is carried out at a pH of less than 3.0.
    Type: Grant
    Filed: November 13, 2002
    Date of Patent: July 6, 2004
    Assignee: The Dow Chemical Company
    Inventors: John Klier, Christopher J. Tucker, Thomas H. Kalantar, Kenneth A. Burdett, Daniel Patrick Green, Luciano Piras, Sergio Schena, Guo-shuh John Lee
  • Patent number: 6743952
    Abstract: The present invention provides an improved process for the production of benzaldehyde with 40-50% selectivity by the catalytic liquid phase air oxidation of toluene using a composite catalytic system comprising salts of iron, cobalt, manganese, molybdenum or nickel as recyclable catalyst, salts of manganese or copper as recyclable co-catalyst and cobalt bromide, sodium bromide, sodium chloride and zinc bromide as promoter.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: June 1, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Mannepalli Lakshmi Kantham, Pentlavalli Sreekanth, Kottapalli Koteshwara Rao, Thella Prathap Kumar, Bhavnari Purna C. Rao, Boyapati Manoranjan Choudary
  • Publication number: 20040049084
    Abstract: A process of the present invention produces phthalaldehyde by allowing at least one compound selected from o-xylylene glycol and o-xylylene oxide to react with nitric acid. The amount of nitric acid is from about 0.2 to about 20 moles per mole of the at least one compound selected from o-xylylene glycol and o-xylylene oxide. The present invention can efficiently produce phthalaldehyde from easily available raw materials.
    Type: Application
    Filed: June 11, 2003
    Publication date: March 11, 2004
    Inventor: Tohru Nakai
  • Patent number: 6670509
    Abstract: A process for oxygenating organic substrates such as aliphatic hydrocarbons has been developed. The process involves contacting the organic substrate with oxygen in the presence of a bicyclo imide promoter and a metal co-catalyst. The process is preferably carried out using sulfolane as the solvent. Optionally, the oxygenated product can be hydrogenated to give the corresponding alcohol which can optionally in turn be dehydrated to provide the corresponding olefin.
    Type: Grant
    Filed: April 11, 2002
    Date of Patent: December 30, 2003
    Assignee: UOP LLC
    Inventors: Paul R. Kurek, David W. House
  • Patent number: 6642419
    Abstract: In the presence of (1) an oxidizing catalyst comprising an imide compound such as N-hydroxyphthalimide, or (2) an oxidizing catalyst comprising such imide compound and a transition metal element-containing compound as a co-oxidizing agent (e. g., oxides, halides, complexes, hetero polyacid salts) a hydrocaron, an alcohol, an aldehyde, or a ketone as a substrate is brought into contact with molecular oxygen for oxidation. In the above-described oxidation process, the water content of the oxidizing reaction system is 200 mol or lower relative to 1 mol of the imide compound. According to the present invention, a substrate is efficiently oxidized with molecular oxygen under mild conditions, and there can be obtained the object compound(s) of high quality.
    Type: Grant
    Filed: October 18, 2000
    Date of Patent: November 4, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroyuki Miura, Hitoshi Watanabe, Tomohide Ina, Hidehiko Nakajima
  • Publication number: 20030187304
    Abstract: The present invention provides an improved process for the production of benzaldehyde with 40-50% selectivity by the catalytic liquid phase air oxidation of toluene using a composite catalytic system comprising salts of iron, cobalt, manganese, molybdenum or nickel as recyclable catalyst, salts of manganese or copper as recyclable co-catalyst and cobalt bromide, sodium bromide, sodium chloride and zinc bromide as promoter.
    Type: Application
    Filed: March 28, 2002
    Publication date: October 2, 2003
    Inventors: Mannepalli Lakshmi Kantham, Pentlavalli Sreekanth, Kottapalli Koteshwara Rao, Thella Prathap Kumar, Bhavnari Purna C. Rao, Boyapati Manoranjan Choudary
  • Patent number: 6590129
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:
    Type: Grant
    Filed: March 19, 2001
    Date of Patent: July 8, 2003
    Assignee: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 6566557
    Abstract: The present invention relates to the preparation of substituted trans-cinnamaldehyde, a natural yellow dye from Phenylpropane derivatives having R2—R3—R4—R5—R6 substitution, wherein R2 to R6 equal or different, being hydrogen or hydroxy or acyl or halogen or alkyl or heterocyclic or aryl or dioxymethylene or alkoxy groups, etc., by oxidizing the said phenylpropane derivatives using a oxidising agent such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or p-chloranil or pyridinium chlorochromate (PCC) or tBuOOH or CrO3 with a catalytic amount of inorganic/organic acid or alumina, celite, and silica gel as a solid support for microwave irradiation and thus substituted trans-cinnamaldehydes, a natural yellow dye, are obtained in high yield ranging from 68-82%.
    Type: Grant
    Filed: March 14, 2001
    Date of Patent: May 20, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Ruchi Dogra
  • Patent number: 6506932
    Abstract: A method for oxidizing an aromatic compound possesssing at least one alkyl substituent by using a catalyst avoids containing a corrosive bromine ion, remains stably without being decomposed even in an oxidizing atmospherfe, and permits reclamation is provided. An aromatic compound possessing at least one alkyl substituent is oxidized by using a catalyst which has at least one kind of element selected from the group consisting of phosphorus, silicon, and germanium as a hetero atom and at least one kind of element selected from the group consisting of molybdenum, tungsten, vanadium, and niobium as a poly atom and comprises a heteropoly-oxometalate anion possessing two defective structure site and at least one kind of element selected from the group of elements of Periods 4˜6 of Groups IB, VA,VIIA, and VIII in the Periodic Table of the Elements.
    Type: Grant
    Filed: November 7, 2001
    Date of Patent: January 14, 2003
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Yasutaka Sumida, Masahiro Wada, Noritaka Mizuno
  • Patent number: 6506943
    Abstract: A process for producing an aldehyde of the invention allows a 1,2-diol (vic-diol) to react with oxygen in the presence of a ruthenium catalyst supported on a carrier to oxidatively cleave a bond between two carbon atoms, where hydroxyl groups are combined with the carbon atoms, to thereby yield a corresponding aldehyde. The carrier includes, for example, an activated carbon. As a catalytic component to be supported on the carrier, dichlorotris(triphenylphosphine)ruthenium(II), and other organic ruthenium complexes, for example, can be used. The invention can efficiently produce a corresponding aldehyde by oxidative cleavage of a 1,2-diol with oxygen.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: January 14, 2003
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6495726
    Abstract: The present invention relates to an improved process for the production of benzaldehyde with 40-50% selectivity comprising by catalytic liquid phase air oxidation of toluene. The process involves providing a continuous flow of air in the presence of a catalyst such as salts of Fe, Co, Mo and Ni, and preferably a co-catalyst such as salts of manganese or copper, a promoter which may also be a bromine source, and a carboxylic acid solvent selected from the group consisting of acetic, propionic, benzoic acids ranging between 0.05 to 0.3 wt. times with respect to toluene, at a temperature ranging between 60-130° C. and pressures in the range of 1-10 bars for a period of 0.5-1.5 hours to obtain benzaldehyde (40-50%) along with other by-products.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: December 17, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Mannepalli Lakshmi Kantam, Boyapati Manoranjan Choudary, Pentlavally Sreekanth, Kottapalli Koteswara Rao, Kantarao Naik, Thella Prathap Kumar, Asad Ali Khan
  • Publication number: 20020188159
    Abstract: The present invention provide a catalyst capable of producing an aromatic aldehyde by gas-phase oxidation of the corresponding alkylbenzene in the presence of a molecular oxygen in high yield, and a method of producing an aromatic aldehyde from the corresponding alkylbenzene in high yield by using the above catalyst.
    Type: Application
    Filed: March 29, 2002
    Publication date: December 12, 2002
    Applicant: NIPPON SHOKUBAI CO., LTD.
    Inventors: Nobuji Kishimoto, Kunika Takahashi, Akiyoshi Nakajima
  • Patent number: 6486357
    Abstract: A method of oxidizing an organic alcohol, wherein the organic alcohol is contacted with a stoichiometric excess of oxygen in the presence of an effective catalytic amount of a maganese-containing octahedral molecular sieve or octahedral layer. Primary alcohols are selectively oxidized to aldehydes, and secondary alcohols are selectively oxidized to ketones.
    Type: Grant
    Filed: August 14, 2001
    Date of Patent: November 26, 2002
    Assignee: The University of Connecticut
    Inventors: Steven L. Suib, Young Chan Son, Amy R. Howell
  • Patent number: 6482991
    Abstract: A method and an apparatus for producing aromatic aldehydes, including benzaldehyde and metatolualdehyde wherein the reaction occurs in the vapor phase. Raw materials and a source of oxygen are fed into a tube reactor. The raw materials may be in a liquid or vapor phase. The reaction to form the aldehyde is catalyzed by suitable solid or liquid catalysts, including copper containing catalysts.
    Type: Grant
    Filed: October 9, 2001
    Date of Patent: November 19, 2002
    Assignee: EagleView Technologies, Inc.
    Inventors: Jack S. Warren, David R. Westphal, Steve J. Zoubek
  • Publication number: 20020143213
    Abstract: A method and an apparatus for producing aromatic aldehydes, including benzaldehyde and metatolualdehyde. Raw materials and a source of oxygen are fed into a tube reactor. The raw materials may be in a liquid or vapor phase. The reaction to form the aldehyde is catalyzed by suitable solid or liquid catalysts, including copper containing catalysts.
    Type: Application
    Filed: October 9, 2001
    Publication date: October 3, 2002
    Inventors: Jack S. Warren, David R. Westphal, Steve J. Zoubek
  • Patent number: 6458737
    Abstract: The present invention has for its object to provide a novel catalyst by use of which methylbenzenes can be oxidized in gaseous phase in the presence of molecular oxygen to give the corresponding aromatic aldehydes in high yields, a process for producing an aromatic aldehyde from the corresponding methylbenzene in a high yield by use of said catalyst, and a process for producing cyclohexanedimethanol which comprises hydrogenating phthalaldehyde among the aromatic aldehydes which can be obtained as above.
    Type: Grant
    Filed: November 13, 2000
    Date of Patent: October 1, 2002
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Nobuji Kishimoto, Isao Nakamura, Yusei Nagamura, Akiyoshi Nakajima, Masashi Hashimoto, Kunika Takahashi
  • Publication number: 20020133045
    Abstract: The present invention relates to the preparation of substituted trans-cinnamaldehyde, a natural yellow dye from Phenylpropane derivatives having R2-R3-R4-R5-R6 substitution, wherein R2 to R6 equal or different, being hydrogen or hydroxy or acyl or halogen or alkyl or heterocyclic or aryl or dioxymethylene or alkoxy groups, etc., by oxidizing the said phenylpropane derivatives using a oxidising agent such as 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) or p-chloranil or pyridinium chlorochromate (PCC) or tBuOOH or or CrO3 with a catalytic amount of inorganic/organic acid or alumina, celite, and silica gel as a solid support for microwave irradiation and thus substituted trans-cinnamaldehydes, a natural yellow dye, are obtained in high yield ranging from 68-82%.
    Type: Application
    Filed: March 14, 2001
    Publication date: September 19, 2002
    Inventors: Arun Kumar Sinha, Bhupendra Prasad Joshi, Ruchi Dogra
  • Patent number: 6350918
    Abstract: Preparing an aldehyde from an alcohol by contacting the alcohol in the presence of oxygen with a catalyst prepared by contacting an intimate mixture containing metal oxide support particles and particles of a catalytically active metal oxide from Groups VA, VIA, or VIIA, with a gaseous stream containing an alcohol to cause metal oxide from the discrete catalytically active metal oxide particles to migrate to the metal oxide support particles and to form a monolayer of catalytically active metal oxide on said metal oxide support particles.
    Type: Grant
    Filed: April 17, 2001
    Date of Patent: February 26, 2002
    Assignee: Lehigh University
    Inventors: Israel E. Wachs, Yeping Cai
  • Patent number: 6297403
    Abstract: A process for the preparation of vinyl, alkynyl, aryl or heteroaryl aldehydes or vinyl, alkynyl, aryl or heteraoryl ketones includes reacting vinyl-, alkynyl-, aryl- and heteroarylmethyl and -methylene compounds with the aid of a mediator and an oxidant, wherein the mediator is selected from the group of the aliphatic, heterocyclic or aromatic NO, or NOH containing compounds.
    Type: Grant
    Filed: January 5, 2000
    Date of Patent: October 2, 2001
    Assignee: Consortium für elektrochemische Industrie GmbH
    Inventors: Elke Fritz-Langhals, Johannes Freudenreich
  • Publication number: 20010018543
    Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound: 1
    Type: Application
    Filed: March 19, 2001
    Publication date: August 30, 2001
    Applicant: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 6281382
    Abstract: The method of oxidizing the alkyl groups of alkylbenzenes using palladium phenanthroline acetate or a palladium acetate with modified phenanthroline ligand catalyst. The palladium acetate catalyst with modified phenanthroline has the following formula: wherein R1 is selected from the group consisting of alkyl groups of from 1 to 3 carbon atoms, OH, and NO2 groups and halogen and hydrogen atoms with at least six of the R1 groups being hydrogen atoms in the ligand.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: August 28, 2001
    Assignee: Georgia Tech Research Corp.
    Inventors: Mark G. White, Alexei V. Iretski